I hope everybody will allow me to expound a bit on something I believe, that young people should engage in adventures when they can as exemplified by Harborless' adventure.
When I first saw his posts concerning sailing without liability insurance, I was disdainful thinking he was an older guy who should know better but then found he is only 23. Realizing his age, my attitude changed as I think he is doing exactly what he should be doing. At his age, the cost of this $2600 boat is probably most of his net worth and the cost of liability insurance is a major deal and his best insurance really is competence. With a little experience and resources, he will realize he needs it and will get it.
I hang out with a bunch of guys my age who are approaching retirement. They all talk about the adventures they hope to have when they are no longer working. Unfortunately, they will no longer be able to walk the Appalachian trail or sail around the world etc as most of us have nearly worked ourselves to death by that time.
When I was his age, I got married and we quit our very good jobs in Houston and without jobs decided to go to Colorado and spend as much time in the wilderness as possible. Everyone thought we were crazy. After camping for 90 days on the Continental divide, she was badly injured in a climbing accident. Fortunately, women talk us into things we otherwise would not do and she had talked me into purchasing a cheap accident policy that was actually expensive for our budget. It paid ALL of her medical expenses, amazing. After her injury, we still camped 30 more days until the snow was collapsing our tent and I went and got an oilfield job in WY.
When my oldest daughter graduated from college, I told her "Don't you dare settle down in a normal job at your age, go have adventures". She took my advice although now I wish she and the BF would settle down. They have managed to do an astonishing amount of very cheap travel all over the world and paid for all of it themselves.
I met a young Australian guy in the Bahamas, he was 24 and had worked for a year in the mines of West AU to make some money and then had "sailboat hitchhiked" across the pacific to Vancouver, then gone across to Quebec and then boat hitched to the bahamas and had found a position on a boat going to Africa and thence back to AU. Someone to admire.
So, I implore Harborless to not give up. This adventure will teach him more useful stuff than any school ever would.

I could write a long book about my crazy adventures when I was young. I settled down at 19, after a serious climbing accident where I almost got killed. I still had various adventures after that, but they were nowhere near as wild. I love sailing, but I go way out of my way to keep it reasonably safe.
I applaud all people in pursuit of adventure and I hope they keep safety in mind at least as much as I do.

I'm only 29 and I already regret that I settled so quickly. No marriage or kids or anything, but two weeks after college graduation I was sitting in a cubicle as a staff accountant. I thought I was getting a leg-up on my freinds who were having adventures/finding themselves/whatever you want to call it (I was real in to horesback riding at the time and many freinds were bumming around the stable all year for nothing pay). I've turned that soul-sucking daily grind as a grunt accountant into a position as Finance Manager of a mid-size aircraft maintenance company, so I can't be bitter as my hard work paid off and I wouldn't own a 35 foot sailboat in Chicago without this job... But, I definitely have a wanderlust that was never satisfied and the more I meet folks that did it, the more I wish I had. My girlfreind spent over two years after college working on tall ships sailing all over the eastern seaboard. She's 32 and spent this winter in chemo and radiation for breast cancer and it gave us both a new outlook on life. We're reminded that we're still very young, but that "when I retire" is so far away and we have no gaurantee of making it that long, let alone being healthy enough for adventure. We hope to move aboard in the Carribbean for an extended time in fall of 2014 - giving us two summers here to save some more money, get married, and get comfortable with boat ownership/maintenance (our current boat is giving me daily reminders of how much work it takes and how little I know, despite learning a lot in the off-seasons when sailing others' boats over the years.) I say kudos to anyone seaking adventure in their 20's - it's such an awesome time in your life, it has been for me, but as I come to the end of them I realize that it was also a time of great freedom and self-discovery that I may not have fully capitalized on...

We are 40s young and continue to have adventures. No kids helps a lot.

Thanks for saying this Tim. Me and my spouse (45 & 50) have always lived an adventurous life. Adventure doesn't always mean we're always racing down a class-IV rapid in an open canoe, or jumping out of an airplane (although a fair smattering of this kind of thing is good). Adventure can be found everywhere.

Lack of kids certainly makes it easier -- this was a choice we made early on. But I also think remaining mostly outside of our acquisition, climb-the-ladder, bigger, faster, more more more, culture has been vital to maintaining our freedom. It's about choices, not age.

You can choose the path laid out for us all, or you can choose to step off. It's always up to you.

I think early 20s is a unique window of opportunity when ones brain is still malleable to profit most from new experiences and most of society is more ready to forgive your "errors". Things that seem cute when young people do them seem creepy when us older types do them. Consider a young guy hanging out in a hostel to an older guy doing the same. My gut reaction to the young guy is "ok, your figuring out what you should do in life" but to the older guy it is "You havent figured it out YET and now your hanging out with the kids sorta sucking the youthful energy out like some sort of aged vampire".

I think early 20s is a unique window of opportunity when ones brain is still malleable to profit most from new experiences and most of society is more ready to forgive your "errors". Things that seem cute when young people do them seem creepy when us older types do them. Consider a young guy hanging out in a hostel to an older guy doing the same. My gut reaction to the young guy is "ok, your figuring out what you should do in life" but to the older guy it is "You havent figured it out YET and now your hanging out with the kids sorta sucking the youthful energy out like some sort of aged vampire".

I also think previous generations did this via joining the military. When I read my 94 yr old dad's journals of his times in the navy I see him learning all about life.

I will note that having kids does not stop you from having adventures at all. Our first child did not slow us down at all and made things much more fun. A small child opens doors that you could never do on your own. In fact, travelling with a small child will enable you to meet far more people than anything else. Yes, you travel differently but you sure experience more travelling with a child.

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